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Raydar

Head of Engineering

Toronto, ON, Canada

$200,000 to $230,000 CAD / year · Full-time

Within 25 km of Vaughan · About 16.5 km from the city centre

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Applications open in a new tab.

Job details

Pay: $200,000 to $230,000 CAD / year
Job type: Full-time
Posted: Nov 5, 2026

Original job description

About the company

Our client is a legal services company.

The role

Raydar is recruiting for this role on behalf of our client. Lead an engineering organization by hiring, developing and managing engineers, setting its technical direction and driving reliable, high-quality software releases. The role combines people leadership with hands-on technical decision-making and includes applying AI to reduce manual effort in internal workflows.

What you'll do

Recruit, grow and manage engineers, with the focus on engineering rather than product management.

Raise the pace of delivery so that priorities turn into dependable, high-quality releases.

Set technical direction across customer-facing applications, internal tools, data, payments and IT systems.

Design AI-driven workflows that cut the manual time needed across several service lines.

Make architecture decisions and contribute hands-on code when the team needs it.

Requirements

What we're looking for

Roughly five to ten years in software development, including time in a leadership capacity.

Proven success in sourcing, coaching and leading software engineers over time.

Solid technical depth for making architecture calls and writing code when needed.

Hands-on background putting AI into operational processes and quantifying the efficiency gains.

Background in establishing development practices that speed up and stabilize shipping cycles.

Experience leading engineering, QA and design staff.

Product judgment and close work with product partners to ship things people use.

Clear, accountable leadership that gives people room to work independently while holding them to results.

Someone who lifts what a group produces and keeps work moving quickly.

Ability to work hybrid in Toronto.

Bonus points

Degree in computer science or engineering.

Experience with TypeScript and PostgreSQL.

Experience building AI or document-processing services.

Experience building a platform that serves multiple products or business lines.

Comfortable in a lean setting, taking on broad responsibility and making quick calls.

Legal background, though not required.

Benefits

Compensation and benefits

Base salary: CAD 200,000 to 230,000 per year

Extended health coverage

Telehealth

Dental and vision coverage

Unlimited paid time off

Location and work model

Toronto, ON, Canada

Hybrid workplace

Full-time

Apply on apply.workable.com About employer

More about this job

Responsibilities

The Head of Engineering will recruit, grow and manage engineers, and set technical direction across customer-facing applications and internal systems. They will make architecture decisions, write code when needed, and build AI-driven workflows that cut manual work.

Requirements

Candidates need five to ten years in software development, including leadership time, and proven success hiring and coaching engineers. They also need solid technical depth, experience putting AI into operational processes, and experience leading engineering, QA and design staff.

Skills

Engineering leadership
Hiring and team building
Coaching software engineers
Architecture design
AI integration in operational processes
Release management
Product collaboration
TypeScript
PostgreSQL
Document-processing services
Platform development
Quality assurance leadership
Process efficiency quantification

Benefits

Extended health coverage
Telehealth
Dental and vision coverage
Unlimited paid time off

Keywords

Head of Engineering
engineering leadership
engineering manager
software development
AI workflows
architecture
TypeScript
PostgreSQL
hybrid Toronto
legal services
legal technology
document processing
release management
team building
technical direction
QA leadership

Seniority

Lead

Perks

Generous paid time off

Tools

TypeScript
PostgreSQL

Languages

English

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